3-Chlorophenol → HCID 89783719, compound

Participants

Reaction Conditions

Reaction Steps

Prepared according to Example 103, NaH as a 60% dispersion in mineral oil (143 μl, 3.29 mmol, Sigma Aldrich), 3-chlorophenol (334 μl, 3.29 mmol, Sigma Aldrich), and 2-(2-chloroquinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 1; 140 mg, 0.470 mmol) and stirring at 85° C. for 17 h. Purification by column chromatography (silica gel, 0 to 60% EtOAc/DCM then 5% MeOH/DCM) providing 2-(2-(3-chlorophenoxy)-8-quinolinyl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (35 mg, 19%). 1H NMR (400 MHz, CDCl3) δ ppm 11.28-11.38 (1H, m) 8.23 (1H, d, J=1.00 Hz) 8.04-8.09 (1H, m) 7.61-7.66 (1H, m) 7.48 (2H, q, J=1.00 Hz) 7.36-7.41 (2H, m) 7.19-7.26 (3H, m) 5.84-6.01 (1H, m) 3.58 (2H, t, J=1.00 Hz) 2.55 (2H, t, J=1.00 Hz). m/z (ESI, +ve) 390.0 (M+H)+.

Provenance & Evidence